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Usage

InChI:InChI=1/C5H9NO4.C5H14NO/c6-3(5(9)10)1-2-4(7)8;1-6(2,3)4-5-7/h3H,1-2,6H2,(H,7,8)(H,9,10);7H,4-5H2,1-3H3/q;+1/p-2/t3-;/m0./s1

Upstream product

• 56-86-0 L-glutamic acid 
• 123-41-1 cholin hydroxide 

Relevant academic research and scientific papers

Soybean oil-based monoacylglycerol synthesis using bio-compatible amino acid ionic liquid as a catalyst at low temperature

Monoacylglycerol (MAG) from edible oil is one kind of green and safe food additive. This project mainly focused on a nontoxic and biodegradable catalyst, amino acid-based ionic liquids (AAILs), for the glycerolysis of soybean oil triacylglycerol (TAG) to prepare MAG at low temperature. Seven AAILs, from arginine, lysine, histidine, tryptophan, or glutamic acid and choline hydroxide, tetramethylhydroxide ammonium, or tetrabutylammonium hydroxide, were successfully synthesized in this work. The effects of substrate ratio, AAIL load, temperature, and reaction time on AAIL-catalyzed the glycerolysis of soybean oil were evaluated. Moreover, the activation energy of MAG formation was explored and reaction mechanism was also proposed. Finally, reaction conditions were optimized by response surface methodology. Results showed that, among all tested AAILs, [TMA][Arg] prepared by arginine (Arg) and tetramethylhydroxide ammonium (TMAOH) showed the outstanding catalytic performance for the glycerolysis of soybean oil. The maximum MAG yield (64.89 ± 1.26%) and TAG conversion (86.31 ± 1.68%) were achieved under the optimized conditions: 105 °C, 0.5 h, [TMA][Arg] load 10%, and substrate molar ratio 1:2 (soybean oil/glycerol). Moreover, the activation energies of MAG formation and TAG conversion were 44.22 kJ/mol and 37.58 kJ/mol, respectively.

Efficient ionic liquid-based platform for multi-enzymatic conversion of carbon dioxide to methanol

Low yields commonly obtained during enzymatic conversion of CO2 to methanol are attributed to low CO2 solubility in water. In this study, four selected ionic liquids with high CO2 solubility were separately added to the multi-enzyme reaction mixture and the yields were compared to the pure aqueous system (control). In an aqueous 20% [CH][Glu] system, yield increased ca. 3.5-fold compared to the control (ca. 5-fold if NADH regeneration was incorporated). Molecular dynamics simulation revealed that CO2 remains for longer in a productive conformation in the enzyme in the presence of [CH][Glu], which explains the marked increase of yield that was also confirmed by isothermal titration calorimetry-lower energy (ΔG) binding of CO2 to FDH. The results suggest that the accessibility of CO2 to the enzyme active site depends on the absence/presence and nature of the ionic liquid, and that the enzyme conformation determines CO2 retention and hence final conversion.

Cholinium-amino acid based ionic liquids: A new method of synthesis and physico-chemical characterization

In the present work we report the synthesis and physico-chemical characterization in terms of the viscosity and density of a wide series of cholinium-amino acid based room temperature ionic liquids ([Ch][AA] RTILs). 18 different amino acids were used to obtain 14 room temperature ILs. Among the most common AAs, only valine did not form an RTIL but it is a liquid above 80 °C. With respect to the methods reported in the literature we propose a synthesis based on potentiometric titration which has several advantages such as shorter preparation time, stoichiometry within ±1%, very high yields (close to 100%), high reproducibility, and no use of organic solvents, thus being more environmentally friendly. We tried to prepare dianionic ILs with some AAs with two potentially ionisable groups but in all cases the salts were solids at room temperature. All the ILs were characterized by 1H NMR to confirm the stoichiometry. Physico-chemical properties such as density, viscosity, refractive index and conductivity were measured as a function of temperature and correlated with empirical equations. The values were compared with the data already reported in the literature for some [Ch][AA] ILs. The thermal expansion coefficient αp and the molar volume Vm were also calculated from the experimental density values. Due to the high number of AAs explored and their structural heterogeneity we have been able to find some interesting correlations between the data obtained and the structural features of the AAs in terms of the alkyl chain length, hydrogen bonding ability, stacking and cyclization. Some parameters were also found to be in good agreement with those reported for other ILs. We think that these data can give an important contribution to the understanding of the structure-property relationship of ILs because they focused on the structural effect of the anions, while most data in the literature are focussed on the cations.

Introducing biobased ionic liquids as the nonaqueous media for enzymatic synthesis of phosphatidylserine

Biobased ionic liquids with cholinium as the cation and amino acids as the anions, which could be prepared from renewable biomaterials by simple neutralization reactions, have recently been described as promising and green solvents. Herein, they were successfully used as the reaction media for enzyme-mediated transphosphatidylation of phosphatidylcholine with l-serine for phosphatidylserine synthesis for the first time. Our results indicated that the highest phosphatidylserine yield of 86.5% was achieved. Moreover, 75% original activity of the enzyme was maintained after being used for 10 batches. The present work could be considered an alternative enzymatic strategy for preparing phosphatidylserine. Additionally, the excellent results make the biobased ionic liquids more promising candidates for use as environmentally friendly solvents in biocatalysis fields.

Ionic liquids from renewable biomaterials: Synthesis, characterization and application in the pretreatment of biomass

A series of room temperature ionic liquids (ILs), in which cholinium acts as the cation and amino acids as the anions, were prepared via a simple and green chemical route, and characterized. Most of the ILs dissolved lignin efficiently and selectively (with solubilities of 140-220 mg of lignin per g of IL). The solubility of xylan in these ILs (which ranged from -1) depended on the nature of the anion, while cellulose was scarcely soluble (-1). In addition, enzymatic hydrolysis of microcrystalline cellulose and rice straw was enhanced significantly after pretreatment using the IL [Ch][Gly].